3,4,5-triethylbenzoic acid | 74660-03-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4,5-triethylbenzoic acid
• CAS: 74660-03-0
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: UVSGKUPBGMJLPF-UHFFFAOYSA-N

物化性质

• 熔点：
  142-143 °C
• 沸点：
  318.1±41.0 °C(Predicted)
• 密度：
  1.029±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4,5-triethylbenzoic acid 在 盐酸 、 sodium hydride 作用下， 反应 3.25h， 生成 ω-(methylsulfonyl)-3,4,5-triethylacetophenone
  参考文献：
  名称：

  2,4-Diamino-5-benzylpyrimidines as antibacterial agents. 8. The 3,4,5-triethyl isostere of trimethoprim. A study of specificity

  摘要：

  3,4,5-Triethylacetophenone was synthesized in 60% yield by a Friedel-Crafts reaction from 4-ethylacetophenone and converted to 2,4-diamino-5-(3,4,5-triethylbenzyl)pyrimidine (2), a trimethoprim (1) isostere, by standard techniques. This compound is more lipophilic than 1 by three log units (log P, octanol/water). Compound 2 was approximately equipotent with 1 in inhibiting Escherichia coli dihydrofolate reductase (DHFR), 2-fold more potent against P. berghei and N. gonorrhoeae DHFR, and 10 and 25 times better an inhibitor of rat and chicken liver DHFR, respectively. Although the 3,4-dimethoxy analogue 19 was 10-fold less inhibitory to E. coli DHFR than 1, it was 3-4 times more potent on the vertebrate isozymes, whereas the diethyl congener 10 followed 19 in its E. coli DHFR binding but was less active on rat and chicken DHFR. Therefore, a significant portion of the selectivity of 1 for bacterial, as opposed to vertebrate, DHFR, involves the methoxy functions. An analysis of the X-ray data on 1 and 2 complexed with chicken DHFR, coupled with kinetic data, led to the conclusion that the difference in binding energies of the methoxy and ethyl compounds probably involve desolvation factors, as well as direct energies of interaction with protein atoms. Thus, one cannot invoke lipophilicity or shape alone in explaining the relationship in properties of 1 and 2.

  DOI：

  10.1021/jm00394a012
• 作为产物：
  描述：

  3,4,5-triethylacetophenone 在 sodium hypobromide 作用下， 生成 3,4,5-triethylbenzoic acid
  参考文献：
  名称：

  The Beckman Rearrangement. VIII. The Influence of Alkyl Groups on the Rates of Rearrangement of Acetophenone Oximes¹

  摘要：

  DOI：

  10.1021/ja01512a027

文献信息

• Optimisation of Tetrahydroisoquinoline-Based Chimeric Microtubule Disruptors
  作者：Wolfgang Dohle、Mathew P. Leese、Fabrice L. Jourdan、Christopher J. Chapman、Ernest Hamel、Eric Ferrandis、Barry V. L. Potter

  DOI：10.1002/cmdc.201402025

  日期：2014.5.12

  Tetrahydroisoquinoline (THIQ)‐based “chimeric” microtubule disruptors were optimised through modification of the N‐benzyl motif, in concert with changes at C3 and C7, resulting in the identification of compounds with improved in vitro antiproliferative activities (e.g. 15: GI50 20 nM in DU‐145). The broad anticancer activity of these novel structures was confirmed in the NCI 60‐cell line assay, with

  基于四氢异喹啉 (THIQ) 的“嵌合”微管破坏剂通过修饰N-苄基基序进行优化，与 C3 和 C7 的变化相一致，从而鉴定出具有改进的体外抗增殖活性的化合物（例如15 : GI 50 20 DU-145 中的n M )。这些新结构的广泛抗癌活性在 NCI 60 细胞系测定中得到证实，12 e , f在 40 n M区域显示 MGM 值。此外，它们作为微管蛋白聚合和秋水仙碱与微管蛋白结合的抑制剂的特性得到证实。化合物15例如，抑制微管蛋白聚合的 IC 50为 1.8 μM，接近临床药物考布他汀 A-4的 IC 50，并且还证明可有效阻断秋水仙碱结合。此外，化合物20b被鉴定为迄今为止该系列中唯一显示出比其相应的氨基磺酸盐更好的体外抗增殖特性和优异的抗微管蛋白数据 (IC 50 =1.6 μM ) 的苯酚。化合物12 F在中空纤维测定中被选择用于体内评价在NCI和显示出非常良好的活性和宽的组织分布，其示出该模板用于进一步开发的值。
• ROTH, BARBARA;AIG, EDWARD, J. MED. CHEM., 30,(1987) N 11, 1998-2004
  作者：ROTH, BARBARA、AIG, EDWARD

  DOI：——

  日期：——
• POLARIZING ELEMENT AND METHOD OF PRODUCING THE SAME
  申请人：Morishima Shinichi

  公开号：US20100134726A1

  公开（公告）日：2010-06-03

  A polarizing element, containing: a transparent support; a light absorption anisotropic layer formed of a dichroic dye composition; and a transparent resin cured layer, with the layers being laminated in this order on the support, and with the composition containing at least one dichroic dye of formula (I) which has nematic mesomorphism but containing no liquid crystalline achromatic compound: wherein R 1 to R 4 are a hydrogen atom or a substituent; R 5 and R 6 are a hydrogen atom or an alkyl group; L 1 represents —N═N—, —CH═N—, —N═CH—, —C(═O)O—, —OC(═O)— or —CH═CH—; A 1 represents a phenyl, naphthyl or aromatic heterocyclic group; B 1 represents a divalent aromatic hydrocarbon or divalent aromatic heterocyclic group; and n is an integer from 1 to 5.
• US8623476B2
  申请人：——

  公开号：US8623476B2

  公开（公告）日：2014-01-07
• The Beckman Rearrangement. VIII. The Influence of Alkyl Groups on the Rates of Rearrangement of Acetophenone Oximes¹
  作者：Patrick J. McNulty、D. E. Pearson

  DOI：10.1021/ja01512a027

  日期：1959.2